The main entrance gate faces Humboldt Street, opening onto the north end of the property. Humboldt was apparently named Kanaka Street for a number of years, after its residents, many of whom came from the Sandwich Islands. The first formal entrance had been added in 1872 and improved in 1882, in preparation for a Royal visit by Princess Louise and the Marquis of Lorne. The ornamental wrought iron gate was set within the brick wall that partially surrounds the Academy's grounds. This wall was built in 1896 to replace the fence that ran along the Humboldt side of the property.
Although the gate has become an unofficial symbol for St. Ann's Academy, many of the students who attended the school over the years never actually passed through its arch. Instead these girls entered the grounds at the Blanshard Street side. By 1922, a wrought iron gate had been placed at this side entrance as well. Old photographs served as the model for the refurbished gate we see today. The curving metalwork holds up the words "St. Ann's Academy". These letters appear almost to float in the centre of the sign, as they are mounted on a fine mesh background that is invisible from only a short distance away.